Groomsmen Proposal Ideas That’ll Make You the Real MVP

If you’re newly engaged, chances are you might have thought that once the proposal bit was over, it would be an effortless flow into your happily-ever-after. Think again!

There’s a whole wedding to be planned and, not to mention, groomsmen that need to be reeled in! Fortunately, there are such things as wedding planners, and the groomsmen proposal aspect – well, that just opens the way for bonding, creativity, and fun with your best buds ahead of your wedding.

When it comes to recruiting groomsmen, it turns out there’s a method to the madness.

Who knew?

Although you can ask simply with no fanfare, what fun would that be really? Your wedding is an exciting event and should be treated as such – that includes placing the needed emphasis on your groomsman proposals.

If you have no idea where to go with this, stay with us. We’ve got it (mostly) all figured out, and, by the end of this post, you will too!

Special handwritten or printed card proposals

We’ll start off with handwritten or printed proposal cards. These work well for a groomsmen proposal because you can make these as personal and creative as you would like. The best part? Your groomsmen will be able to save their proposal card and remember this special occasion during which they played such an important role!

Handmade or custom card

Handmade items, including cards, have a special feel that lets the receiver know you really did put some thought into them. Your groomsmen won’t need to be artistically inclined to appreciate the thought that went into the invite. Incorporate elements that stand out about your friendship, and you’ll have a round of yeses in no time!

Mustache groomsmen proposal cards

“I mustache you an important question, and I hope you will say yes!” Who really will be able to turn down a proposal that starts like this? Some mustache-inspired groomsmen cards come with a fake mustache inside the card along with an invite for the groomsman to send a photo back to the groom wearing the faux facial hair to signal his acceptance. This one is guaranteed to fire up some laughs!

“Suit Up” groomsmen proposal cards

Time to suit up boys, it’s a special occasion! Indeed, it is, and a card that says something simple like, “Suit up. Will you be my groomsman?” is sure to get you some prompt responses.

Funny groomsmen proposal cards

“I know of a great party with an open bar…” and you’re invited! Just like that, your groomsmen will be lured in. Chances are, they won’t mind a bit that the open bar will be at your wedding reception!

Groomsmen proposal scratch-off lottery-style tickets

Have your groomsmen take a bit of a gamble with some lottery-style scratch-off cards that are hard to resist trying. In this case, a chance to be your groomsman or best man will be the big prize once they scratch the card, which you can even personalize with a photo of your face!

To-the-point groomsmen proposal card

Would you rather skip the long-winded conversation that can sometimes accompany trying to convince your friends to be your groomsmen? Get a proposal card that says it for you: “I want you to be my groomsman. Thanks for saying yes. Great talk!”

Draft your groomsmen card

Your wedding is a big deal. Draft your groomsmen much like you would the members of a special task force, because let’s be real… you’re going to need a great team to help you get your wedding to run smoothly from start to finish!

A scratch-off card

Other than lottery-style scratch-off tickets, you can get other types of scratch-off cards to do the asking for you. Choose one that is as unique as your friendship, and make sure there’s lots of humor added in!

Goodie boxes

Groomsmen proposal box (DIY)

A great groomsmen proposal idea revolves around filling some gift boxes with neat gifts like shot glasses, a handy pocket knife, and other bits and pieces while including a note asking your groomsmen whether they’re down to support you on your big day. Of course, they will be! You can even make a party of it and have them all open their boxes together. The celebration will begin the moment you pop the cap of your favorite booze and put some use to those shot glasses!

Prepackaged groomsmen proposal box

Would you rather just get a gift that you don’t have to do much shopping around for? Go for a groomsmen proposal gift set that can include things like sunglasses, watches, minimalist wallets, flasks, cigar cutters or holders, corkscrews or openers, and other options all in a keepsake box. You can choose how much or how little you want each box to contain, and prices vary. This is something your groomsmen will definitely smile about - that and your amazing proposal!

Insider tip: Still undecided about where you want to have your wedding? Consider a Sandals all-inclusive wedding where you can customize your ceremony in the Caribbean just the way you would like!

Things they can wear

Get them groomsmen watches

Pick up some stylish and durable watches your best guys will be able to sport at your wedding and gift them as part of your groomsman proposal. This will help ensure all the guys will be on time for your wedding too!

Insider tip: Look for watches that come in their own eco-friendly boxes, so you can easily give them out to your groomsmen.

Personalized groomsmen sunglasses

Outside of a proposal box, sunglasses might still come in handy. You can get a few pairs for your groomsmen to sport on your big day. This will be very much needed if you’re tying the knot with a sunny all-inclusive resort wedding in the Caribbean!

Send them underwear

Underwear will be an unexpected find in the mail that will catch the attention of your groomsmen to be. Get some pairs that have "groomsman" or "best man” wording on them and include a funny card with your request. Wait by the phone - they’ll surely be calling quickly with a reaction!

Gift them socks they can wear on your wedding day

A good pair of socks never hurt anyone, and they certainly won’t do any harm to the friendship you share with your groomsmen. Your invite can either be written on the socks, or in a note that accompanies this gift, but either way, these unique socks will definitely add a pop of color to your wedding!

Personalized cufflinks

Personalized cuff links are an elegant gift that works for just about any occasion. They’ll serve two purposes in this instance. First, they’ll show some appreciation to your groomsmen, and second, they’ll add a little zing to your friends’ formal wear on your big day.

A custom pullover hoodie

Pullovers always come in handy, and your groomsmen will get a kick out of customized ones that make your request without having to say a word. There are many different colors and quotes to choose from for your groomsmen's hoodies. You all can think of a fun way to incorporate them into your wedding.

Groomsmen accessory gift sets

A groomsman gift set is a cool way to gift your groomsmen with a few small items that complement each other - like a pocket square and tie bar combo. You can choose whether to get them all matching sets, or whether you want to give each of your friends something that suits their taste. Include notes in each box to let your boys know what it’s all about.

Custom pocket watches

Friends who’ve stood the test of time are most certainly worthwhile picks to be your groomsmen. You can show your appreciation with some classic pocket watches. Get the watches monogrammed for a personal touch. Box and wrap these up with a handwritten note to make your request!

Bow ties or regular ties

Ties and bow ties will be needed on your wedding day. You can plan for this in advance by gifting your groomsmen matching pieces that’ll go well with their attire on the day. Of course, they won’t know that part yet, and will only find out when you drop the big question!

Superhero shirts

Few things say I appreciate our friendship more than superhero shirts, especially for friends who can’t get enough of Marvel or DC movies. You can get a shirt for each groomsman, and you can all wear these under your wedding attire for a Clark Kent moment that will definitely go down in history.

Insider tip: Want to have a vacation and wedding in one? You can have a free Sandals wedding if you stay at the resort for a minimum of 3 nights!

Things they can eat

Take them to an awesome restaurant

When was the last time you headed out with your bros to a great dining spot? If you have to think about your answer, then an evening at a stand-out restaurant might be the perfect backdrop for your groomsman proposal. You’ll have an amazing meal, and the odds will be in your favor for yeses all around!

A customized box of dry rub seasonings

Your groomsmen won’t be expecting this, but they’ll love this box of seasoning options, especially if they’re foodies! If you’re a bit of an “underrated chef” yourself, you can even create a homemade seasoning mix they can take home with them along with your amazing news.

Beef jerky with groomsmen proposal card

A beef jerky proposal is definitely not something you hear about every day, but it's a flavorful present you can consider if you really want to entice your friends. You can make it yourself, or find a premium brand online… Either way, beef jerky with a side of whiskey, beer, or chocolate will be a sure win.

A box of donuts

Donuts make people happy, which can translate to automatic yeses for your proposal. This is especially so if the donuts are hand delivered at an opportune time when you can just ambush your friends with the question. This is best done with several donut boxes though, and you can personalize them to cater to each friend.

Hot sauce or hot pepper oil

You can make your own hot sauce or hot pepper oil fairly easily, and your friends just may be curious enough to try it. Why not host a small tasting event around your special hot sauces? This will definitely spice up your proposal. Make sure everyone gets to leave with their own bottle of hot sauce or hot pepper oil - you can even create a customized label with your big question!

Things they can eat or drink from

Challenge them to ‘Chug A Beer’

A round of ‘Chug A Beer’ will take you all back to your college days! You can even include customized labels for this option. The names of your groomsmen and your wedding date can be printed on the labels of a six-pack of beer that will then be delivered to their houses. Chugging a beer (video proof required!) is all they’ll need to do to let you know that they accept!

Tip: Once you receive all your ‘yes’ video clips, you can compile them into a fun video that you can share with your new groomsmen team or play at your reception!

Put their face on a flask

Who can say no to a personalized caricature flask? No one, really! All jokes aside though, your friends will appreciate a personalized flask with a creative caricature as part of your groomsmen proposal - it’ll be something that will forever remind them of your beautiful, big moment.

Baseball bat mugs

Are you and your friends baseball fans? If you are, some baseball mugs made out of real baseball bats will be a good conversation starter as you get ready to ask your boys to stand by your side on your wedding day. Each mug comes with a personal message, so you might not have to say much as the wording will invite them to be your groomsmen in plain and simple terms.

Never let him forget an embarrassing moment

An approaching wedding is as good a time as any to pull some files, which may or may not paint a flattering picture. Pick a photo, any photo of your friends, either individually or in a group, and have the words ‘will you be my groomsmen’ printed on them in a creative way. Then, get a vendor to put these photos on glasses that you can gift your friends. Choose a few humorous photos or a single photo that will have everyone in stitches!

A bottle of booze with a custom label

A few bottles of custom-labeled booze will go down well with your groomsmen-to-be. Not only will you be able to pop the big question, but you’ll be able to have a fun evening with your friends that can include barbecued treats or other tasty appetizers.

Do a shot together

Personalized shot glasses are a sure win. Gift these in a box set with a pint of their favorite alcohol, or yours. You can all meet up to present the gifts in person, and with everyone in the same space, you’ll be able to do a celebratory shot together.

A personalized beer mug

A personalized beer mug, much like a shot glass, will remind you of all the amazing times you’ve had together. This will be a welcome gift for a crew that loves beer, and while you’re all sipping from the 25-ounce stein, you can present your question in a lighthearted atmosphere.

Custom coffee mugs

For the non-alcohol-drinking crowd, custom coffee mugs out of the blue will be enough to have them questioning the occasion. After you hand them over, you can sit everyone down and ask them to be the groomsmen on your special day.

A bottle of wine

A good bottle of wine always comes in handy. For your proposal, you can create a personalized label with each of the names of your potential groomsmen written alongside the date of your wedding. This gift won’t require much talking, and your boys will be able to keep the bottle as a memento.

Insider tip: Still trying to figure out a location for your wedding? Sandals' wedding inclusions make it possible to choose from a range of incredible locations, including an Over-the-Water Chapel!

Manly things for around the home

Toss them the question

Personalized footballs offer an opportunity to add some playfulness to your pitch. There won’t be any room for fumbles as you put together the all-star team that will take you smoothly into the end zone on your wedding day. Each personalized football can include one groomsman’s name, your wedding date, and the role they will fulfill on the day.

A cigar with a custom label

Add an exotic touch to your groomsman proposal by including some personalized cigars with labels you can design yourself. Make this into a fun outing by doing something you all love to do together. That way, you can surprise them with the boxed cigars and see their reactions for yourself!

Send them a humidor with cigars

Or you can take things up a notch and get a humidor with cigars for each groomsman. This is a step up in the luxury department, and you can make your request known with a note letting them know you’ll all be saving the cigars to celebrate later – as in, on your wedding day.

Travel toiletry bags

Toiletry bags will be something your groomsmen might actually be able to use if you’re planning an all-inclusive destination wedding! Even if you’re not planning on traveling, a good toiletry bag will come in handy for the getting-ready suite you’ll likely book out ahead of the wedding.

Custom pocketknives

Pocket knives always come in handy, and you can get some custom ones for your groomsmen as a prelude to your big question. This will be especially well-received if your bachelor event has something to do with the outdoors … like say, a camping trip. Go big with this gift and get some fancy ones that come with fire starters and LED flashlights.

Personalized weekender bags

Weekender bags are one of those items that always seem to disappear when you need them most. Spare your groomsmen from having to hunt for theirs ahead of your bachelor party or destination wedding and get them some custom duffle bags. Include cards asking them to accompany you on your “next incredible adventure”! Your groomsmen duffle bags can include details on their role in the wedding on the exterior!

Custom bottle opener

One can never have too many bottle openers. Well, scratch that. A person can never have enough bottle openers that actually work right! Get your groomsmen some keychains with credit card-sized/shaped openers, or even 50 caliber bullet bottle openers. There are many fun options that will add to the appeal of your groomsman request and get you a full round of yeses. For added effect, have custom engravings applied!

Monogrammed beach towels

Having a beach wedding? A monogrammed beach towel will be great for your groomsmen, even if they don’t know it yet! They certainly will get the idea when you gift them some great monogrammed towels with all the information, they’ll need to figure out what all the fuss is about!

Custom playing cards

Playing cards always come in handy, and you and your groomsmen can make good use of them at your bachelor party and beyond. You can choose any design to create a custom pack of cards for your boys, and you’ll even be able to include that extra special date!

Custom groomsmen shaving kit

Help your groomsmen stay in tip-top shape by gifting them a shaving kit. Get some good quality kits that will really inspire your team to put in their best effort on your wedding day, like one that leaves room for you to get a razor handle monogrammed, for example.

Personalized luggage tag

Luggage tags will be the perfect gift for your groomsmen if they’ll accompanying you and your bride-to-be somewhere tropical for your wedding. You can add a cool photo or your friends’ initials or nicknames to make this gift a little more personal.

Insider tip: Speaking of traveling, the only thing better than a Sandals wedding, that includes everything you’ll need for your wedding event, is a Sandals honeymoon that comes with everything you need for romance! Sandals honeymoon packages include ‘a bubbly welcome’, special turndown service, a chance to wake up to wedded bliss (including breakfast in bed on a morning of your choice), and so much more!

Other cool options

A DIY gift

Some of the most popular DIY groomsmen proposal gifts include wood slice serving boards, leather mason jar sleeves, beef jerky, salsa, homemade hot sauce, shaving cream, framed and customized maps marking experiences, and more. When going the DIY route, you can easily gift all your groomsmen with the same gift, while switching things up a bit for your best man. However, you decide to go about your DIY groomsmen gift project, your boys will certainly appreciate the effort.

Draft your groomsmen onto your team (humor included)

Make a show of getting all your best buds involved in your wedding by conducting a playful draft that will let every one of your groomsmen know just how much you value their friendship. It’s perfectly alright to take some digs at them even as you recruit them to be part of your wedding team, NBA Draft-style. Be sure to mention their talents and strengths as well.

Make them a groomsmen caricature

Caricatures are artistic, fairly realistic, and something you can hold onto and appreciate basically until the paper they’re printed on falls apart. Get a custom group groomsmen caricature done and either have it printed out or text it to them as you make the ultimate wedding request.

Make a video for them

Compile a special video that will highlight each of your groomsmen in a comedic and fun way. You can go all out for this one and even create a short film asking your buddies to be there for you on your wedding day. When the video is complete, send it to them and wait for the happy responses!

Send them a funny text

A humorous text message out of the blue asking your friends to be your groomsmen will definitely come as a huge surprise. This is a simple and easy way to get the message across, and all you’ll need to do is confirm that each of your guys will be available on your wedding date.

Surprise them out on the green

If you and your guys are into golf, you can set up an unexpected groomsmen proposal right out on the green. None of them will be expecting it, and it’ll be hard to say no through the huge smiles on their faces.

Take them to a high-end go-kart racetrack

Go-karting is always good fun, and you can set up a day to head out and make some rounds on the course with your boys. After racing around, stuffing yourselves silly with drinks and food, and comparing race stats, you can ask them collectively to be your groomsmen!

Get them tickets to a sporting event

If going to big games is something you and your friends like doing together, you can set this up ahead of your big ask. Somewhere between rooting for your favorite team and downing beers and hot dogs, you can slip in the question about being your groomsmen!

Take them to a cigar lounge

Treat your friends to some great cigars at a cigar lounge as special tokens of appreciation. In this private space, you all can relive old memories… right before you deliver the big news. Ask the proprietor to include a note with their cigar choices that will invite them to be there for you on your wedding day.

Set up a pub crawl

The only thing better than the average pub crawl with friends is a pub crawl that ends with one of the bunch - you - inviting your best buddies to be your groomsmen. You can choose a day to meet with each friend or do it all together with a party pass that will give you access to drink specials.

Insider tip: Planning on getting married at Sandals? Skip the wedding planning jitters and enjoy your time in the Caribbean to the fullest knowing your dedicated Sandals wedding planner has everything under control.

Take them to a gun range

Blazing guns and proposals don’t necessarily go hand in hand but taking your friends to a gun range and spontaneously asking them to be your groomsmen will definitely be something they’ll never forget.

Get down on one knee… again!

If you want to get some serious laughs out of your friends, get down on one knee and hilariously ask them to be your groomsmen, much like you did with your fiancé! Your friends definitely won’t let you hear the end of this, but it’ll all be good fun!

Serenade them

You don’t have to be a singer to execute this one - in fact, it’ll probably be a whole lot funnier if you’re not! If you are though, serenading your groomsmen with a song you can write yourself to ask them to have your back on your wedding day will come across as sentimental and well thought out. Either way, it’ll be entertaining!

A celebrity shout out

Yes, a celebrity shout-out! Even if you don’t know any celebs personally, this is entirely possible. Look into a service that will allow you to get your friends’ favorite celeb to pop the question on your behalf. Most of these services work via apps, and all you’ll need to do is provide the text and wait until the video is sent to you. Once you receive it, you’ll be able to share the wealth with your groomsmen!

Treasure hunt

Adventure anyone? For old time's sake, set up a treasure hunt where your friends can find some real goodies, and then eventually, a card asking them to be your groomsmen. There’s no need to make this challenge hard, just set it up in a casual hang-out spot and include a poster board at the starting point with a clue to the location of the next hint.

Groomsmen proposal getaway

Of all the groomsmen proposals out there, nothing will beat asking your friends while on the getaway of a lifetime. There are amazing locations you can head out to in the Caribbean, including islands like Jamaica, The Bahamas, Saint Lucia, Antigua, Grenada, and Barbados. One thing all these islands have in common is that you’ll be able to find the best adults-only all-inclusive resorts. White sand beaches, greenery for miles, and luxurious Sandals accommodations will all be the perfect ingredients for an out-of-this-world groomsman proposal (or destination wedding)!

These groomsmen proposal ideas will be hard to turn down…

As they should be! Weddings work best when you have people involved who’ve really been there for you through the good times and bad, and the above-mentioned ideas will definitely help you reel in those special men in your life for your big day!

Insider tip: Want to see why guests can’t stop raving about their incredible Sandals weddings? Check out these amazing Sandals real wedding photos!